title: Monoamine oxidase inhibitory activity of 3,5-biaryl-4,5-dihydro-1H-pyrazole-1-carboxylate derivatives.
abstract: Ethyl and phenyl carbamate derivatives of pyrazoline (3a-3h) were synthesized and tested for their MAO inhibitory activity. All the compounds were found to be selective towards MAO-A. Phenyl carbamates (3e-3h) were better than ethyl carbamates (3a-3d) and displayed the best selectivity index. Compound 3f (KiMAO-A; 4.96 ± 0.21 nM) was found to be equally potent as that of standard drug, Moclobemide (KiMAO-A; 5.01 ± 0.13 nM) but with best selectivity index (8.86 × 10(-5)). Molecular docking studies with R &S conformer of 3f revealed S-enantiomer is better than R-enantiomer as reported earlier by other groups. It is proposed that VdW's radii of the substitution (bulkiness) in ring B determine the potency of phenyl carbamates.
authors.affiliation: Department of Pharmaceutical Sciences, Birla Institute of Technology, Mesra, Ranchi, Jharkhand 835 215, India.
authors.forename: B
authors.initials: B
authors.lastname: Vishnu Nayak
authors.forename: S
authors.initials: S
authors.lastname: Ciftci-Yabanoglu
authors.forename: Surender Singh
authors.initials: SS
authors.lastname: Jadav
authors.forename: Monika
authors.initials: M
authors.lastname: Jagrat
authors.forename: Barij N
authors.initials: BN
authors.lastname: Sinha
authors.forename: G
authors.initials: G
authors.lastname: Ucar
authors.forename: Venkatesan
authors.initials: V
authors.lastname: Jayaprakash
mesh_terms: D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure; D008995:Monoamine Oxidase / Q000378:metabolism*; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D008996:Monoamine Oxidase Inhibitors; D011720:Pyrazoles; D008995:Monoamine Oxidase
keywords: Carbamates; Human monoamine oxidase; Inhibitors; MAO; Molecular docking; Pyrazolines; SAR; back-bone; bb; hMAO; human MAO; monoamine oxidase; rMAO; rat MAO; sc; side-chain; structure–activity-relationship